822-36-6

Basic information

• Product Name: 2-Methylimidazole-4-sulfonic acid
• Synonyms: 1H-Imidazole, 4-methyl-;1H-Imidazole,4-methyl;4(5)-Methylglyoxaline;4(Or 5)-Methylimidazole;4-Me-i;4-methyl-1(3)H-imidazole;4-methyl-1h-imidazol;4-methyl-imidazol
• CAS NO: 822-36-6
• Molecular Formula: C₄H₆N₂
• Molecular Weight: 82.1
• EINECS: 212-497-3
• Product Categories: Imidazol&Benzimidazole;Miscellaneous;Imidaxoles;Building Blocks;Heterocyclic Building Blocks;Imidazoles;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 822-36-6.mol
• Article Data: 22

Chemical Properties

• Melting Point: 44-47 °C(lit.)
• Boiling Point: 263 °C(lit.)
• Flash Point: >230 °F
• Appearance: Reddish-brown to green to brown/Powder
• Density: 1.02
• Vapor Pressure: 0.0172mmHg at 25°C
• Refractive Index: 1.5037
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble, clear, colorless to yellow (50 mg/mL)
• PKA: pK1:7.55(＋1) (25°C)
• Water Solubility: Soluble in water.
• BRN: 1453
• CAS DataBase Reference: 2-Methylimidazole-4-sulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylimidazole-4-sulfonic acid(822-36-6)
• EPA Substance Registry System: 2-Methylimidazole-4-sulfonic acid(822-36-6)

Safety Data

• Hazard Codes: C
• Statements: 21/22-34-22
• Safety Statements: 26-36/37/39-45-25
• RIDADR: UN 3263 8/PG 3
• WGK Germany: 2
• RTECS: NI7350000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 822-36-6(Hazardous Substances Data)

Usage

Chemical Properties

Slightly yellow chunks. soluble in water and ethanol.

Uses

Different sources of media describe the Uses of 822-36-6 differently. You can refer to the following data:
1. 4-Methylimidazole is a monomethylated imidazole that can be used as a building block in the preparation of a wide range of biologically active compounds. 4-Methylimidazole is a product which results f rom the interaction of reducing sugars with ammonia. 4-Methylimidazole showed convulsant activity in animals and is listed as a possible carcinogen.
2. 4-Methylimidazole is used for the curing agent of epoxy resin, the main raw material of medicine cimetidine. It can also be used for synthesis of antibacterial agent.

Preparation

4-Methylimidazole is synthesized by the reaction of glyoxal, acetaldehyde and ammonia. Another method to synthesize the compound is by catalytic dehydrogenation of imidazoline derivatives. 4-Methylimidazole may be synthesized from propanol and formamide, by catalytic cyclization of bisformamidipropane or by photolysis of alkenyltetrazole derived from alkenes by sequential epoxidation, ring opening and dehydration (NTP, 2007).

Definition

ChEBI: 4-methylimidazole is imidazole substituted at position 4 by a methyl group. It has a role as a carcinogenic agent and a reaction intermediate.

General Description

4(5)-Methylimidazole was quantified in coffee by GC-MS method.

Purification Methods

Recrystallise 4-methylimidazole from *benzene or pet ether. It has m 56o after sublimation. The picrate has m 162-163.5o (from EtOH). [Beilstein 23 II 60, 23 III/IV 597, 23/5 V 89.]

InChI:InChI=1/C4H6N2/c1-4-2-5-3-6-4/h2-3H,1H3,(H,5,6)

Synthetic route

hexamethylenetetramine (100-97-0) + 2-oxopropanal (78-98-8) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With ammonium acetate; acetic acid at 103℃; for 0.0666667h; Microwave irradiation;	76%

formaldehyd (50-00-0) + dihydroxyacetone (96-26-4) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With zinc hydroxide; ammonia

formaldehyd (50-00-0) + Acetol acetate (592-20-1) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With ammonium hydroxide; copper diacetate

D-Fructose (57-48-7) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With zinc hydroxide; ammonia
With zinc hydroxide; ammonia

D-Fructose (57-48-7) → 4-methyl-1H-imidazole (822-36-6) + 2-hydroxymethyl-4-methylimidazole (872-79-7)

Conditions	Yield
With ammonium hydroxide; manganese(II) sulfate

D-Mannose (3458-28-4) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With zinc hydroxide; ammonia

L-rhamnose (6014-42-2) → 4-methyl-1H-imidazole (822-36-6) + 2,4-Dimethylimidazole (930-62-1)

Conditions	Yield
With zinc hydroxide; ammonia

L-xylose (609-06-3) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With zinc hydroxide; ammonia

L-arabinose (5328-37-0) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With zinc hydroxide; ammonia

L-Rhamnose (3615-41-6) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With zinc hydroxide; ammonia

D-glucose (50-99-7) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With zinc hydroxide; ammonia
With zinc hydroxide; ammonia
With zinc hydroxide; ammonia at 100℃;
With zinc hydroxide; ammonium hydroxide; formaldehyd at 90℃; under 4413.05 - 5884.06 Torr;

D-Galactose (59-23-4) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With zinc hydroxide; ammonia

dihydroxyacetone (96-26-4) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With zinc hydroxide; ammonia

4-(chloromethyl)-1H-imidazole hydrochloride (38585-61-4) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With palladium on activated charcoal; ethanol Hydrogenation;

2-methyl-3H-imidazole-4-carboxylic acid (1457-58-5) → 4-methyl-1H-imidazole (822-36-6)

formaldehyd (50-00-0) + 2-oxopropanal (78-98-8) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With zinc hydroxide; ammonia; water
With zinc hydroxide; ammonia

Maltose (133-99-3, 490-37-9, 2152-98-9, 4482-75-1, 5965-66-2, 13299-27-9, 13360-52-6, 14641-93-1, 15548-43-3, 16462-44-5, 16984-36-4, 16984-38-6, 20869-27-6, 22688-72-8, 27452-49-9, 29276-55-9, 30608-12-9, 34481-13-5, 37169-60-1, 37169-64-5, 64234-01-1, 64234-02-2, 75281-88-8, 80446-85-1, 84413-57-0, 92344-56-4, 93221-87-5, 93301-77-0, 94799-29-8, 100427-98-3, 100428-00-0, 101312-82-7, 102046-24-2, 102046-25-3, 109432-00-0, 109432-02-2, 109432-04-4, 109432-08-8, 135268-49-4, 138231-26-2, 140461-59-2, 145414-22-8, 145414-26-2, 146339-75-5, 146339-76-6, 149116-55-2) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With zinc hydroxide; ammonia

D-(+)-lactose (63-42-3) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With zinc hydroxide; ammonia

pyrrole (109-97-7) + 4-Methylimidazolate anion (70019-89-5, 196413-36-2) → 4-methyl-1H-imidazole (822-36-6) + pyrrolide anion (23303-09-5)

Conditions	Yield
at 600℃; under 0.8 - 2.4 Torr; Thermodynamic data; intrinsic gas phase acidity (acid dissociation energy) is measured as a model for strong interactions in proteins and enzymes;

N,N-bis(trimethylsilyl)formamide (15500-60-4) + methyllithium (917-54-4) + tosylmethylisocyanate lithium → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
1) THF, -78 deg C, 30 min, 2a) -78 deg C, 30 min, 2b) -78 to 0 deg C, 2 h, 2c) RT, 16 h; Yield given. Multistep reaction;

acetaldehyde (75-07-0) + tosylmethylisocyanate lithium → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With lithium hexamethyldisilazane 1) THF, -60 to -30 deg C, 20 min, 2a) -78 deg C, 30 min, 2b) -78 to 0 deg C, 2 h, 2c) RT, 16 h; Yield given. Multistep reaction;

dimethyl sulfoxide (67-68-5) + 1-(trimethylsilyl)-4-methylimidazole (119352-64-6) → 4-methyl-1H-imidazole (822-36-6) + Hexamethyldisiloxane (107-46-0) + 4-Methyl-1-methylsulfanylmethyl-1H-imidazole (73844-89-0)

Conditions	Yield
at 140 - 180℃;

2,2-Dimethyl-propionic acid 4-nitro-phenyl ester; compound with 4-methyl-1H-imidazole → 4-methyl-1H-imidazole (822-36-6) + 4-nitrophenyl pivalate (4195-17-9)

Conditions	Yield
With 2-(cyclohexylamino)ethanesulfonic acid In acetonitrile at 27℃; Equilibrium constant;

N-(aminomethyl)benzamide (67908-02-5) + 2-oxopropanal (78-98-8) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With water; acetic acid 1.) 4 h, 50 deg C; Yield given. Multistep reaction;

formaldehyd (50-00-0) + 2-ethoxyprop-2-enal (2648-49-9) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With hydrogenchloride; ammonia 1.) water, 35-40 deg C, 4 h, 2.) water, 70 deg C, 30 min, other reagent: ammonium carbonate; Yield given. Multistep reaction;

glucose monohydrate (56119-27-8) → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With formaldehyd; zinc hydroxide carbonate; phosphoric acid; sulfuric acid; ammonia 1.) H2O, 100 deg C, 1 h, 2.) H2O, 95 - 97 deg C, 30 min; 20 deg C, 20 min; Yield given; Multistep reaction;

2-bromo-4-methyl-imidazole → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
With sodium sulfite

4-methyl-1,3-dihydro-imidazole-2-thione (3247-70-9) + nitric acid (7697-37-2) → 4-methyl-1H-imidazole (822-36-6)

sulfuric acid (7664-93-9) + 4-methyl-1(3)H-imidazole-2-sulfinic acid → 4-methyl-1H-imidazole (822-36-6)

Conditions	Yield
an der Luft;

Pentafluoropyridine (700-16-3) + 4-methyl-1H-imidazole (822-36-6) → 1-(2,3,5,6-tetrafluoropyridyl)-4-methylimidazole

Conditions	Yield
In tetrahydrofuran at 20℃; for 20h;	100%

4-methyl-1H-imidazole (822-36-6) + methyl isocyanate (624-83-9) → 4-Methyl-imidazole-1-carboxylic acid methylamide (87864-86-6)

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	99%

4-methyl-1H-imidazole (822-36-6) + trityl chloride (76-83-5) → 4-methyl-1-trityl-1H-imidazole (82594-80-7)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 3.5h;	98.2%
With triethylamine In N,N-dimethyl-formamide for 3.5h;	98.2%
With triethylamine In N,N-dimethyl-formamide for 3.5h;	98.2%

4-methyl-1H-imidazole (822-36-6) + p-chlorphenylisocyanate (104-12-1) → 4-Methyl-imidazole-1-carboxylic acid (4-chloro-phenyl)-amide (87864-85-5)

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	98%

4-methyl-1H-imidazole (822-36-6) + C9H9BrN2O2 → C13H14N4O2

Conditions	Yield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 0.133333h; Inert atmosphere;	98%
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 5h; Inert atmosphere;	98%
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 5h; Inert atmosphere;	98%

4-methyl-1H-imidazole (822-36-6) + phenylacetyl chloride (103-80-0) → 4-Methyl-1-(phenylacetyl)imidazole (123331-32-8)

Conditions	Yield
In dichloromethane for 1.5h; Ambient temperature;	97%

2,2':6,2''-terpyridine (1148-79-4) + 4-methyl-1H-imidazole (822-36-6) + copper(II) tetrafluroborate hexahydrate → {(2,2':6',2''-terpyridine)(4-methylimidazole)(H2O)(BF4)copper(II)}(BF4)

Conditions	Yield
In methanol to a soln. of the Cu-salt and the imidazole in methanol is added dropwise a methanolic soln. of terpyridine with stirring; ether is then allowed to diffuse slowly into the soln., blue crystals are obtained in a few days, washed, dried, elem. anal.;	97%

4-methyl-1H-imidazole (822-36-6) + [3-bromo-5-(trifluoromethyl)phenyl]amine (54962-75-3) → 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (641571-11-1)

Conditions	Yield
With copper(l) iodide; (+)-D-glucosamine hydrochloride; caesium carbonate In water; dimethyl sulfoxide at 90℃; for 12h; Temperature; Concentration;	96.18%
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In toluene; tert-butyl alcohol at 120℃; for 8h; Inert atmosphere;	91%
With copper(l) iodide; 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethan-1-one; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 18h; Inert atmosphere; Sealed tube;	91%

bromobenzene (108-86-1) + 4-methyl-1H-imidazole (822-36-6) → 1-phenyl-4-methyl-1H-imidazole

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 5h; Inert atmosphere;	96%
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 5h; Inert atmosphere; regioselective reaction;	95%
With aluminum oxide; potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In xylene at 130 - 140℃; for 15h;	91%
With potassium carbonate; copper(I) bromide In nitrobenzene for 18h; Heating;	8.8%
With 2-[(dimethylamino)methyl]benzenethiolato-copper(I); potassium carbonate In 1-methyl-pyrrolidin-2-one at 160℃; for 16h; Inert atmosphere;	59 %Chromat.

iodobenzene (591-50-4) + 4-methyl-1H-imidazole (822-36-6) → 1-phenyl-4-methyl-1H-imidazole

Conditions	Yield
With C46H48Cu2Fe4I2Te4; lithium tert-butoxide at 85℃; for 12h; Catalytic behavior; Ullmann-Goldberg Substitution; Sealed tube; Green chemistry;	96%
With aluminum oxide; potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In xylene at 130 - 140℃; for 13h;	95%
With potassium carbonate; copper(l) chloride In water at 80℃; for 24h; Inert atmosphere;	90%
With copper(l) iodide; caesium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine In N,N-dimethyl-formamide at 110℃; for 24h;	77%
With copper(l) iodide; sodium hydroxide In dimethyl sulfoxide at 120℃; for 20h;	70%

vinyl acetate (108-05-4) + 4-methyl-1H-imidazole (822-36-6) → 1-(4-methyl-imidazol-1-yl)-ethyl acetate

Conditions	Yield
In various solvent(s) at 50℃; for 48h; Markovnikov's addition;	96%
With [bmIm]OH at 50℃; for 4h; Markovnikov addition;	88%
With D-aminoacylase from Escherichia coli (EC 3.5.1.81) In hexane at 50℃; for 96h;	80%
With potassium tert-butylate In acetonitrile at 20℃; for 12h; regioselective reaction;	75%
With Thermomyces lanuginosus lipase; potassium carbonate In dimethyl sulfoxide at 50℃; for 0.5h; Flow reactor; Enzymatic reaction;	20%

4-methyl-1H-imidazole (822-36-6) + Di-tert-butyl acetylenedicarboxylate (66086-33-7) + triphenylphosphine (603-35-0) → di-tert-butyl 2-(4-methylimidazol-1-yl)-3-(triphenylphosphoranylidene)butanedioate

Conditions	Yield
In ethyl acetate at 20℃; for 24h;	96%
In ethyl acetate at 27℃; Kinetics; Temperature; Solvent;

4-methyl-1H-imidazole (822-36-6) → 4-methylimidazolium pentaborate

Conditions	Yield
With boric acid In methanol; water for 1h;	96%

4-methyl-1H-imidazole (822-36-6) + phenyl isocyanate (103-71-9) → 4-methyl-1-(phenylcarbamoyl)imidazole (87864-84-4)

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	95%

4-methyl-1H-imidazole (822-36-6) + dimethylamino sulfonyl chloride (13360-57-1) → 4-methylimidazole-1-sulfonic acid dimethylamide (151161-77-2)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 16h;	95%
With triethylamine	61%
With triethylamine In dichloromethane Inert atmosphere;

4-methyl-1H-imidazole (822-36-6) + Rh2(N,N'-di-p-tolylformamidinate)2(trifluoroacetate)2(H2O)2*0.5benzene (105164-41-8) → Rh2(N,N'-di-p-tolylformamidinate)2(trifluoroacetate)2(4-methylimidazole)2 (105164-44-1)

Conditions	Yield
In diethyl ether the Et2O soln. of water adduct was stirred with the imidazole (15min); addn. of hexane, slow evapn. of the solvent; elem. anal.;	95%

4-methyl-1H-imidazole (822-36-6) + trimethyltin(IV)chloride (1066-45-1) → [bis(4-methylimidazole)trimethyltin(IV)]chloride (205391-68-0)

Conditions	Yield
In diethyl ether N2-atmosphere; stirring (0°C, 1 h); crystn. (Et2O); elem. anal.;	95%

4-methyl-1H-imidazole (822-36-6) + 3-(5-bromo-6-methoxypyridin-2-yl)-5-phenyl-5,6-dihydro-4H-1,2,4-oxadiazine → 3-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-5-phenyl-5,6-dihydro-4H-1,2,4-oxadiazine

Conditions	Yield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 18.05h; Inert atmosphere;	95%

4-methyl-1H-imidazole (822-36-6) + copper(ll) bromide (7789-45-9) → dibromidotetrakis(4-methylimidazole)copper(II)

Conditions	Yield
In methanol at 20℃; for 2h;	95%

4-methyl-1H-imidazole (822-36-6) + dimethyltin dichloride (753-73-1) → bis(4-methylimidazole)dimethyldichlorotin(IV) (205391-71-5, 205391-91-9)

Conditions	Yield
In diethyl ether stirring (room temp., 10 h); filtering, washing (Et2O), crystn. (CH2Cl2); elem. anal.;	94%

3-(benzyloxy)phenyl bromide (53087-13-1) + 4-methyl-1H-imidazole (822-36-6) → 1-(3-(benzyloxy)phenyl)-4-methyl-1H-imidazole (1351990-64-1)

Conditions	Yield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 5h; Inert atmosphere; regioselective reaction;	94%

ethyl bromide (74-96-4) + 4-methyl-1H-imidazole (822-36-6) + methyl iodide (74-88-4) → 3,4-dimethyl-1-ethylimidazolium bis(fluorosulfonyl)imide

Conditions	Yield
Stage #1: 4-methyl-1H-imidazole; methyl iodide With potassium carbonate In acetone at 20℃; for 20h; Stage #2: ethyl bromide In toluene at 80℃; for 16h; Stage #3: With potassium bis(fluorosulfuryl)amide In tetrahydrofuran at 75℃; for 5h; Inert atmosphere;	94%

4-methyl-1H-imidazole (822-36-6) + 2-chloro-6-methoxy-3-nitropyridine (38533-61-8) → 6-methoxy-2-(4-methyl-1H-imidazol-1-yl)-3-nitropyridine (1156499-27-2)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; Product distribution / selectivity;	93%
Stage #1: 4-methyl-1H-imidazole With dmap In chloroform at 0℃; for 0.166667h; Stage #2: With triethylamine In chloroform at 0℃; for 0.166667h; Stage #3: 2-chloro-6-methoxy-3-nitropyridine In chloroform at 0 - 20℃;	93%
With dmap; triethylamine In chloroform at 0 - 20℃;	93%

o-fluorobromobenzene (1072-85-1) + 4-methyl-1H-imidazole (822-36-6) → 1-(2-fluorophenyl)-4-methyl-1H-imidazole (1351990-67-4)

Conditions	Yield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 5h; Inert atmosphere; regioselective reaction;	93%

3-(4-bromophenyl)-1,4-diazaspiro[4.4]non-3-en-2-one + 4-methyl-1H-imidazole (822-36-6) → 3-(4-(4-methyl-1H-imidazol-1-yl)phenyl)-1,4-diazaspiro[4.4]non-3-en-2-one (1132817-67-4)

Conditions	Yield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 130℃; for 6h; Inert atmosphere; regioselective reaction;	93%
With potassium phosphate; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane; toluene at 115℃; for 12h; Sealed tube; Inert atmosphere;	85%

4-methyl-1H-imidazole (822-36-6) + C17H21BrO3 → C21H26N2O3

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	92.78%
With potassium carbonate In acetonitrile at 20℃;	92.78%
With potassium carbonate In acetonitrile at 20℃; for 24h;	82.35%

4-methyl-1H-imidazole (822-36-6) + acetyl chloride (75-36-5) → 1-(4-methyl-1H-imidazol-1-yl)ethan-1-one (61553-60-4)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 12h;	92%
In chloroform; toluene for 1h; Ambient temperature;
With triethylamine In acetonotrile at 20℃;
With triethylamine In acetonitrile at 0 - 20℃;
With triethylamine In acetonitrile at 0 - 20℃; for 1h; Inert atmosphere;

4-methyl-1H-imidazole (822-36-6) + 4-methoxyphenyl-acetic chloride (4693-91-8) → 1-<(4-Methoxyphenyl)acetyl>-4-methylimidazole (123331-33-9)

Conditions	Yield
In dichloromethane for 1.5h; Ambient temperature;	92%

4-methyl-1H-imidazole (822-36-6) + 2-(mesyloxy)-1-[2-[(tert-butoxycarbonyl)amino]phenyl]ethane (193806-50-7) → 2-(5-methyl-1H-imidazol-1-yl)-1-[2-[(tert-butoxycarbonyl)-amino]phenyl]ethane (892393-34-9) + 2-(4-methyl-1H-imidazol-1-yl)-1-[2-[(tert-butoxycarbonyl)-amino]phenyl]ethane (892393-33-8) + 1-(tert-butoxycarbonyl)indoline (143262-10-6)

Conditions	Yield
Stage #1: 4-methyl-1H-imidazole With sodium hydride In N,N-dimethyl-formamide at 25℃; for 0.5h; Stage #2: 2-(mesyloxy)-1-[2-[(tert-butoxycarbonyl)amino]phenyl]ethane In N,N-dimethyl-formamide at 25℃; for 2.5h; Product distribution / selectivity;	A n/a B n/a C 92%
In dichloromethane; toluene at 25 - 80℃; for 71h; Product distribution / selectivity;	A n/a B n/a C 22%

4-methyl-1H-imidazole (822-36-6) + copper(II) bis(trifluoromethanesulfonate) hexahydrate → tetrakis(5-methyl-1H-imidazole-κN3)copper(II) bis(trifluoromethanesulfonate) (667909-43-5)

Conditions	Yield
With 2,2-dimethoxypropane In acetonitrile soln. of 4-methyl-1H-imidazole and Cu(CF3SO3)2*6H2O (4:1 mol) in MeCN with 5% dimethoxypropane stirred at room temp. for 2 h; Et2O added dropwise until pptn. started, stored in refrigerator for 2 d;	92%

Upstream product

• 50-00-0 formaldehyd 
• 96-26-4 dihydroxyacetone 
• 592-20-1 Acetol acetate 
• 3458-28-4 D-Mannose 
• 6014-42-2 L-rhamnose 
• 609-06-3 L-xylose 
• 5328-37-0 L-arabinose 
• 3615-41-6 L-Rhamnose 
• 50-99-7 D-glucose 
• 59-23-4 D-Galactose 
• 63-42-3 D-(+)-lactose 
• 15500-60-4 N,N-bis(trimethylsilyl)formamide 
• 917-54-4 methyllithium 
• 3247-70-9 4-methyl-1,3-dihydro-imidazole-2-thione 

Downstream Products

• 548481-51-2 1,2-bis-isovalerylamino-propane 
• 15813-08-8 5-bromo-4-methyl-1H-imidazole 
• 219814-29-6 2,4-dibromo-5-methyl-1H-imidazole 
• 344416-79-1 3-(4-methyl-imidazol-1-yl)-benzonitrile 
• 339526-03-3 methyl 2-(4-methyl-1H-1-imidazolyl) acetate 
• 29636-87-1 4⁽⁵⁾-methyl-5⁽⁴⁾-hydroxymethylimidazole 
• 379229-01-3 2-(5-methyl-1H-imidazol-1-yl)ethanol 
• 150587-22-7 5-methyl-1-phenyl-1H-imidazole 
• 641571-11-1 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline 
• 870837-41-5 5-bromo-2-(4-methyl-1H-imidazol-1-yl)benzonitrile 
• 102791-94-6 5-(4-methylimidazol-1-yl)-2-nitrotoluene 
• 910654-28-3 4-methyl-1-(2-(trifluoromethyl)-4-nitrophenyl)-1H-imidazole 
• 92-83-1 xanthene 

Relevant articles and documents

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METHOD FOR PRODUCING HETEROAROMATIC CARBOXYLIC ACID

PROBLEM TO BE SOLVED: To provide a method for producing heteroaromatic carboxylic acids at good yields, when producing the heteroaromatic carboxylic acids by the oxidation of methyl-substituted heteroaromatic compounds. SOLUTION: A method for producing a heteroaromatic carboxylic acid includes oxidizing a methyl-substituted heteroaromatic compound, having one or more methyl groups on a heteroaromatic ring, with a basic compound and a permanganate. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Pd-catalyzed coupling reaction of fluorinated propargyl amidines with aryl iodides

Catalyzed by ligand free Pd(OAc)2, 2,5-disubstituted imidazole was prepared in good yield by the reaction of fluorinated propargyl amidines with iodoarene. Mechanistic studies indicated that this transformation occurs through a nitropalladation-reductive elimination pathway. The Royal Society of Chemistry.